Cool. very cool. great progress on this.
A couple of things if you want 'em. The resolution of the field texture is lower than that of the rest of the work. Sharpen it up, or put the trees like the ones you've scattered over the ones from the textures.
I would expect more of a defined road into the the main gate. it looks odd the cobbles just stop at the gate and then there's a mud road. Maybe have some road texture that isn't in such a high contrast to the cobbles? Also if the time line is the equivalent of medieval times, then Romans where before making decent roads.
I was watching a program on Castles last night, your general castle with stone masons takes about 10 years. With your map, it would be nice to see more evidence of this time passed for such a sizeable town. So more smaller communities outside the walls on the north side along with some more fields perhaps?
Lastly, some of the buildings look like they are 'crushed' along the north wall, it doesn't look like they are placed naturally nor aligned to the wall itself.
Just some observations.
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I haven't done any real thinking about this place so you'll have free reign.
